6-[(2R,3R,4S,5R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-chloro-acetoxy)-4-hydroxy-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

Base Information

Chemical Name:6-[(2R,3R,4S,5R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-chloro-acetoxy)-4-hydroxy-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester
CAS No.:211801-65-9
Molecular Formula:C₃₆H₄₉ClO₁₁Si
Molecular Weight:721.317
Hs Code.:

6-[(2R,3R,4S,5R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-chloro-acetoxy)-4-hydroxy-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

Synonyms:6-[(2R,3R,4S,5R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-chloro-acetoxy)-4-hydroxy-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

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Chemical Property of 6-[(2R,3R,4S,5R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-chloro-acetoxy)-4-hydroxy-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

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Technology Process of 6-[(2R,3R,4S,5R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-chloro-acetoxy)-4-hydroxy-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

There total 9 articles about 6-[(2R,3R,4S,5R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-chloro-acetoxy)-4-hydroxy-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

: 211801-64-8
6-[(2R,3R,4S,5S,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-chloro-acetoxy)-4-(4-methoxy-benzyloxy)-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

: 211801-65-9
6-[(2R,3R,4S,5R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-chloro-acetoxy)-4-hydroxy-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at -20 ℃;
DOI:10.1021/ja9813616

Reference yield:

: 1152-39-2,28244-98-6,121523-95-3,131488-68-1
p-methylphenyl-1-thio-β-D-galactopyranoside

: 211801-65-9
6-[(2R,3R,4S,5R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-chloro-acetoxy)-4-hydroxy-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / imidazole / dimethylformamide

2: 1.) Bu₂SnO, 2.) Bu₄NI / 1.) toluene, benzene, reflux, 2.) DMF, 60 deg C

3: 52 percent / Et₃N / CH₂Cl₂ / -20 - 20 °C

4: 83 percent / DCC, 4-DMAP / CH₂Cl₂

5: 1.) N-iodosuccinimide, TMSOTf, 4A molecular sieves, 2.) HgBr₂ / 1.) MeCN, from -20 deg C to RT, 2.) toluene, MeNO₂, 60 deg C

6: 97 percent / CF₃CO₂H / CH₂Cl₂ / -20 °C

With 1H-imidazole; dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; mercury dibromide; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja9813616

Reference yield:

: 4547-43-7
methyl 6-hydroxycaproate

: 211801-65-9
6-[(2R,3R,4S,5R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-chloro-acetoxy)-4-hydroxy-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) N-iodosuccinimide, TMSOTf, 4A molecular sieves, 2.) HgBr₂ / 1.) MeCN, from -20 deg C to RT, 2.) toluene, MeNO₂, 60 deg C

2: 97 percent / CF₃CO₂H / CH₂Cl₂ / -20 °C

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; trifluoroacetic acid; mercury dibromide; In dichloromethane;
DOI:10.1021/ja9813616